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Anna L. Adams and Derek Macmillan Investigation of peptide thioester formation via N[RIGHTWARDS ARROW]Se acyl transfer Journal of Peptide Science 19

Version of Record online: 7 JAN 2013 | DOI: 10.1002/psc.2469

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A fast, new route to peptide thioesters is presented, using selenocysteine at the C-terminus of peptides prepared from solid-phase peptide synthesis. Thioester formation is initiated via an N[RIGHTWARDS ARROW]Se acyl shift and can occur at lower temperatures and in shorter time scales than previously seen when using cysteine in this way. This strategy also has been shown to accelerate the cyclization of an antimicrobial peptide.

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